WO2012032907A1 - 粘着シート、及び電子デバイス - Google Patents

粘着シート、及び電子デバイス Download PDF

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Publication number
WO2012032907A1
WO2012032907A1 PCT/JP2011/068651 JP2011068651W WO2012032907A1 WO 2012032907 A1 WO2012032907 A1 WO 2012032907A1 JP 2011068651 W JP2011068651 W JP 2011068651W WO 2012032907 A1 WO2012032907 A1 WO 2012032907A1
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Prior art keywords
sensitive adhesive
pressure
gas barrier
layer
adhesive sheet
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PCT/JP2011/068651
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English (en)
French (fr)
Japanese (ja)
Inventor
和恵 上村
由美子 網野
悠太 鈴木
小野　義友
恵美 中島
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リンテック株式会社
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Application filed by リンテック株式会社 filed Critical リンテック株式会社
Priority to CN201180042769.4A priority Critical patent/CN103154172B/zh
Priority to US13/820,837 priority patent/US20130209800A1/en
Priority to EP11823386.5A priority patent/EP2615144B1/en
Priority to KR1020137005722A priority patent/KR101886455B1/ko
Priority to JP2012532918A priority patent/JP5422055B2/ja
Publication of WO2012032907A1 publication Critical patent/WO2012032907A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/22—Plastics; Metallised plastics
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J7/00—Adhesives in the form of films or foils
    • C09J7/20—Adhesives in the form of films or foils characterised by their carriers
    • C09J7/29—Laminated material
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
    • C08G77/62—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
    • C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J121/00—Adhesives based on unspecified rubbers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/80—Constructional details
    • H10K50/84—Passivation; Containers; Encapsulations
    • H10K50/844—Encapsulations
    • H10K50/8445—Encapsulations multilayered coatings having a repetitive structure, e.g. having multiple organic-inorganic bilayers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
    • C09J183/16—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/318—Applications of adhesives in processes or use of adhesives in the form of films or foils for the production of liquid crystal displays
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2203/00—Applications of adhesives in processes or use of adhesives in the form of films or foils
    • C09J2203/326—Applications of adhesives in processes or use of adhesives in the form of films or foils for bonding electronic components such as wafers, chips or semiconductors
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2421/00—Presence of unspecified rubber
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2433/00—Presence of (meth)acrylic polymer
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J2483/00—Presence of polysiloxane
    • C09J2483/006—Presence of polysiloxane in the substrate
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/28—Web or sheet containing structurally defined element or component and having an adhesive outermost layer
    • Y10T428/2848—Three or more layers

Definitions

  • the present invention relates to an adhesive sheet and an electronic device provided with the adhesive sheet as an electronic device member.
  • organic electronics has attracted attention as a technology that can form displays, circuits, batteries, etc. on flexible plastic substrates at low temperatures close to room temperature using coating and printing processes. It is being advanced.
  • a light-emitting element used for a liquid crystal display or an electroluminescence (EL) display an organic EL element capable of high-luminance light emission by low-voltage direct current drive has attracted attention.
  • EL electroluminescence
  • use of a transparent plastic film as a substrate having electrodes has been studied in order to realize a reduction in thickness, weight, flexibility, and the like.
  • this organic EL element has a problem that when it is driven for a certain period of time, light emission characteristics such as light emission luminance, light emission efficiency, and light emission uniformity are deteriorated compared to the initial stage. Possible causes of this problem include oxidation of the electrode due to oxygen or water vapor entering the organic EL element, modification of organic matter, oxidative decomposition of the organic material due to heat during driving, and the like.
  • a plastic film used as a substrate has a problem that it easily transmits oxygen, water vapor, and the like, and easily deteriorates an organic EL element.
  • an adhesive sheet for an organic device for example, an adhesive film using a polyisobutylene-based resin as an adhesive layer is disclosed (see Patent Document 2).
  • the adhesive layer of Patent Document 2 is vulnerable to high temperatures, ultraviolet rays, and the like, and the organic EL elements and devices are exposed to high temperature or ultraviolet irradiation due to long-time driving or driving environment, so that the resin itself of the adhesive layer deteriorates.
  • the performance of the adhesive film may be degraded and the organic EL element may be deteriorated accordingly.
  • the present invention has been made in view of solving the above-described problems, and provides an adhesive sheet excellent in gas barrier properties, bending resistance, and transparency, and an electronic device including the adhesive sheet as a member for an electronic device. With the goal.
  • the gas barrier layer constituting the pressure-sensitive adhesive sheet is composed of a material containing at least oxygen atoms and silicon atoms, and the ratio of oxygen atoms, nitrogen atoms and silicon atoms in the surface layer portion of the gas barrier layer, and It has been found that an adhesive sheet having a film density in a specific range can solve the above problems.
  • a pressure-sensitive adhesive sheet having at least a gas barrier layer and a pressure-sensitive adhesive layer on a substrate, wherein the gas barrier layer is made of a material containing at least oxygen atoms and silicon atoms, and is a surface layer of the gas barrier layer
  • the oxygen atom content ratio is 60 to 75%
  • the nitrogen atom content ratio is 0 to 10%
  • the silicon atom content ratio is 25 to 35% with respect to the total amount of oxygen atoms, nitrogen atoms, and silicon atoms.
  • a pressure-sensitive adhesive sheet having a film density of 2.4 to 4.0 g / cm 3 in a surface layer portion of the gas barrier layer.
  • the pressure-sensitive adhesive sheet according to the above [1], wherein the material constituting the gas barrier layer comprises a polysilazane compound.
  • the polysilazane compound is perhydropolysilazane.
  • the ions are ionized at least one gas selected from the group consisting of hydrogen, nitrogen, oxygen, argon, helium, neon, xenon, and krypton. .
  • the pressure-sensitive adhesive sheet of the present invention is excellent in gas barrier properties, bending resistance, and transparency. Therefore, the adhesive sheet of this invention can be used suitably for electronic devices, such as a display and a solar cell.
  • the pressure-sensitive adhesive sheet of the present invention has at least a gas barrier layer and a pressure-sensitive adhesive layer on a substrate.
  • Drawing 1 is a figure showing an example of composition of an adhesive sheet of the present invention.
  • the adhesive sheet of this invention has a base material, a gas barrier layer, and an adhesive layer at least, if an adhesive layer exists in the outermost layer, the order to laminate
  • FIG. 1 (A1) there is a pressure-sensitive adhesive sheet 1 in which a gas barrier layer 3 is laminated on one side of a substrate 2 and a pressure-sensitive adhesive layer 4 is laminated on the gas barrier layer 3.
  • the adhesive layer 4 is laminated
  • the pressure-sensitive adhesive layer 4b is provided on the surface of the opposite base material, It is good also as the adhesive sheet 1b which has an adhesive layer on both surfaces.
  • a pressure-sensitive adhesive is provided between two gas barrier layers 3a and 3b including a gas barrier layer 3a laminated on one side of the substrate 2a and a gas barrier layer 3b laminated on one side of the substrate 2b.
  • the adhesive sheet 1c which provides the layer 4a and has the adhesive layers 4b and 4c on the opposite side to the surface in which the gas barrier layer of the base materials 2a and 2b was provided, respectively.
  • the pressure-sensitive adhesive sheet 1c serves not only to bond the two gas barrier layers 3a and 3b to the pressure-sensitive adhesive layer 4a but also to absorb the shock and protect the gas barrier layers 3a and 3b when an impact is applied from the outside. be able to.
  • “other layers” other than the base material, the gas barrier layer, and the pressure-sensitive adhesive layer may be provided.
  • the position where other layers are laminated is not particularly limited, and is appropriately selected according to the role of each layer.
  • (1) base material, (2) gas barrier layer, (3) pressure-sensitive adhesive layer, and (4) other layers constituting the pressure-sensitive adhesive sheet will be sequentially described.
  • the substrate of the present invention is not particularly limited as long as it is a material other than the polysilazane compound and has a self-supporting property and meets the object of the present invention.
  • a base material to be used for example, polyimide, polyamide, polyamideimide, polyphenylene ether, polyether ketone, polyether ether ketone, polyolefin, polyester, polycarbonate, polysulfone, polyethersulfone, polyphenylene sulfide, polyarylate, acrylic resin, A cycloolefin type polymer, an aromatic polymer, etc. are mentioned.
  • polyester, polyamide, or cycloolefin polymer is preferable, and polyester or cycloolefin polymer is more preferable because of excellent transparency and versatility.
  • the polyester polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polyarylate, and the like.
  • the polyamide wholly aromatic polyamide, nylon 6, nylon 66, nylon copolymer and the like.
  • cycloolefin polymers include norbornene polymers, monocyclic olefin polymers, cyclic conjugated diene polymers, vinyl alicyclic hydrocarbon polymers, hydrides thereof, and the like.
  • Specific examples of products include Apel (ethylene-cycloolefin copolymer manufactured by Mitsui Chemicals), Arton (norbornene polymer manufactured by JSR), Zeonore (norbornene polymer manufactured by Nippon Zeon), and the like. It is done.
  • the thickness of the substrate is not particularly limited, but is preferably 0.5 to 500 ⁇ m, more preferably 1 to 200 ⁇ m, and more preferably 10 to 100 ⁇ m.
  • the gas barrier layer of the pressure-sensitive adhesive sheet of the present invention satisfies at least the following requirements (a) to (c).
  • (A) It is comprised from the material containing an oxygen atom and a silicon atom at least.
  • (B) The proportion of oxygen atoms present is 60 to 75%, the proportion of nitrogen atoms is 0 to 10%, and the presence of silicon atoms with respect to the total amount of oxygen atoms, nitrogen atoms and silicon atoms in the surface layer portion of the gas barrier layer. The proportion is 25 to 35%.
  • the film density in the surface layer portion of the gas barrier layer is 2.4 to 4.0 g / cm 3 .
  • the pressure-sensitive adhesive sheet of the present invention has excellent gas barrier properties because the permeability of gas such as water vapor is remarkably small.
  • the water vapor transmission rate of the gas barrier layer is preferably 1.0 g / m 2 / day or less, more preferably 0.5 g / m 2 / day or less, and still more preferably 0.000 or less in an atmosphere of 40 ° C. and 90% relative humidity. 1 g / m 2 / day or less.
  • the water vapor transmission rate can be measured using a known gas transmission rate measuring device, and in the present invention, it means a value measured by the method described in Examples (the same applies hereinafter).
  • the pressure-sensitive adhesive sheet of the present invention is excellent in bending resistance, it is possible to maintain the gas barrier property even when folding or the like is performed. This can be confirmed from the fact that the partial gas barrier layer is not deteriorated and the water vapor transmission rate hardly decreases.
  • the pressure-sensitive adhesive sheet of the present invention is excellent in maintaining gas barrier properties even after folding, as compared with the case where an inorganic film having the same thickness is laminated as a gas barrier layer.
  • a polysilazane compound As a material satisfying the above requirement (a), a polysilazane compound is preferable from the viewpoint of improving gas barrier properties, bending resistance, and transparency.
  • the polysilazane compound is a polymer having a repeating unit containing a —Si—N— bond in the molecule, and specifically includes a compound having a repeating unit represented by the formula (1).
  • n represents an arbitrary natural number.
  • Rx, Ry, and Rz each independently represent a hydrogen atom, an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, unsubstituted or substituted Represents a non-hydrolyzable group such as an aryl group having a group or an alkylsilyl group;
  • alkyl group of the unsubstituted or substituted alkyl group examples include, for example, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, t-butyl group, n
  • alkyl groups having 1 to 10 carbon atoms such as -pentyl group, isopentyl group, neopentyl group, n-hexyl group, n-heptyl group and n-octyl group.
  • Examples of the unsubstituted or substituted cycloalkyl group include cycloalkyl groups having 3 to 10 carbon atoms such as a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.
  • Examples of the alkenyl group of an unsubstituted or substituted alkenyl group include, for example, a vinyl group, a 1-propylenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, and a 3-butenyl group. Examples include 2 to 10 alkenynyl groups.
  • substituents for the alkyl group, cycloalkyl group and alkenyl group include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; hydroxyl group; thiol group; epoxy group; glycidoxy group; (meth) acryloyloxy group
  • halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom
  • hydroxyl group such as hydroxyl group; thiol group; epoxy group; glycidoxy group; (meth) acryloyloxy group
  • An unsubstituted or substituted aryl group such as a phenyl group, a 4-methylphenyl group, and a 4-chlorophenyl group;
  • aryl group of the unsubstituted or substituted aryl group examples include aryl groups having 6 to 10 carbon atoms such as a phenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • substituents for these aryl groups there are halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom; alkyl groups having 1 to 6 carbon atoms such as methyl group and ethyl group; carbon such as methoxy group and ethoxy group Nitro group; cyano group; hydroxyl group; thiol group; eboxy group; glycidoxy group; (meth) acryloyloxy group; unsubstituted phenyl group, 4-methylphenyl group, 4-chlorophenyl group, etc. Or the aryl group which has a substituent; etc. are mentioned.
  • alkylsilyl group examples include trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, tri-t-butylsilyl group, methyldiethylsilyl group, dimethylsilyl group, diethylsilyl group, methylsilyl group, and ethylsilyl group.
  • Rx, Ry, and Rz a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, or a phenyl group is preferable, and a hydrogen atom is more preferable.
  • Examples of the polysilazane compound having a repeating unit represented by the formula (1) include inorganic polysilazanes in which Rx, Ry, and Rz are all hydrogen atoms, and organic polysilazanes in which at least one of Rx, Ry, and Rz is not a hydrogen atom. There may be.
  • the inorganic polysilazane is a perhydro having a linear structure having a repeating unit represented by the following formula (2), a molecular weight of 690 to 2000, and 3 to 10 SiH 3 groups in one molecule.
  • Polysilazane (see Japanese Patent Publication No. 63-16325), perhydropolysilazane having a linear structure and a branched structure represented by the following formula (3), and perhydropolysilazane represented by the following formula (5) Examples thereof include perhydropolysilazane having a polysilazane structure, a linear structure, a branched structure and a cyclic structure in the molecule.
  • Examples of the organic polysilazane include the following compounds (i) to (v).
  • Rx ′ is an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, unsubstituted or substituted
  • (Ii) — (Rx′SiHNRz ′) — (Rz ′) is an unsubstituted or substituted alkyl group, an unsubstituted or substituted cycloalkyl group, an unsubstituted or substituted alkenyl group, unsubstituted or A compound having a cyclic structure mainly having a degree of polymerization of 3 to 5 with a repeating unit of an aryl group having a substituent or an alkylsilyl group.
  • Rx ′ and Ry ′ represent the same meaning as described above, e and f represent an arbitrary natural number, and Y 3 represents a hydrogen atom or a group represented by the following formula (8).
  • the organic polysilazane can be produced by a conventionally known method. As a specific production method, for example, by reacting ammonia or a primary amine with a reaction product of a halogenosilane compound having an unsubstituted or substituted group represented by the following formula (9) and a secondary amine. Organic polysilazanes can be synthesized. Secondary amine and primary amine used, depending on the structure of the polysilazane compound of interest, may be selected.
  • m represents 2 or 3
  • X represents a halogen atom
  • R 1 represents a substituent of any one of the aforementioned Rx, Ry, Rz, Rx ′, Ry ′, and Rz ′. .
  • a modified polysilazane compound can also be used as the polysilazane compound.
  • the modified polysilazane include, for example, a polymetallosilazane containing a metal atom (the metal atom may be crosslinked), and repeating units of [(SiH 2 ) g (NH) h )] and [(SiH 2 ) i O] (wherein g, h and i are each independently 1, 2 or 3), polysiloxazan (Japanese Patent Laid-Open No. 62-195024), and polysilazane with a poron compound.
  • a polyborosilazane produced by reaction Japanese Patent Laid-Open No.
  • a polymetallosilazane produced by reacting polysilazane and a metal alkoxide Japanese Patent Laid-Open No. 63-81122
  • an inorganic silazane high polymer Modified polysilazanes (JP-A-1-138108, etc.), copolymerized silazanes obtained by introducing organic components into polysilazane (JP-A-2-175726, etc.), polysilazanes Low temperature ceramicized polysilazanes (JP-A-5-238827, etc.), silicon alkoxide-added polysilazanes (JP-A-5-238827), glycidol-added polysilazanes (specially) Kaihei 6-122852), acetylacetonato complex-added polysilazane (JP-A-6-306329), metal carboxylate-added polysilazane (JP-A-6-299118, etc.), these polys
  • modified polysilazane obtained by adding alcohol such as methanol or hexamethyldisilazane to the terminal N atom to perhydropolysilazane ( JP-A-5-345 26, JP-A No. 4-63833 JP), and the like.
  • the polysilazane compound inorganic polysilazane in which Rx, Ry, and Rz are all hydrogen atoms, and organic polysilazane in which at least one of Rx, Ry, and Rz is not a hydrogen atom are preferable, and easy availability and excellent gas barrier properties are obtained. From the viewpoint of forming a layer having an inorganic polysilazane, inorganic polysilazane is more preferable, and perhydropolysilazane is more preferable.
  • the number average molecular weight of the polysilazane compound to be used is not particularly limited, but is preferably 100 to 50,000. In the present invention, the number average molecular weight (Mn) is a value calculated as a polystyrene conversion value by gel permeation chromatography (GPC method) (hereinafter the same).
  • the polysilazane compound a commercially available product as a glass coating material or the like can be used as it is.
  • the gas barrier layer may contain other components in addition to the polysilazane compound as long as the object of the present invention is not impaired. Examples of other components include curing agents, other polymers, anti-aging agents, light stabilizers, and flame retardants.
  • the content of the polysilazane compound in the gas barrier layer is preferably 50% by mass or more, more preferably 70% by mass or more, in all materials constituting the gas barrier layer, from the viewpoint of forming a gas barrier layer having excellent gas barrier properties. Preferably it is 85 mass% or more, More preferably, it is substantially 100 mass%.
  • the method for forming the gas barrier layer is not particularly limited.
  • a gas barrier layer-forming solution containing at least one polysilazane compound, and optionally other components, a solvent, and the like is applied onto the substrate.
  • the method of forming the obtained coating film by dry-drying moderately is mentioned. It does not specifically limit as a coating method, The method of using well-known coating apparatuses, such as a spin coater, a knife coater, and a gravure coater, is mentioned. Further, in order to improve gas barrier properties of the dried and the gas barrier layer of the resulting coating film, it is preferred to heat the coating. Heating is preferably performed at 80 to 150 ° C.
  • the gas barrier layer can also be formed by bringing a plasma polymerizable silazane compound gas such as dimethyldisilazane, tetramethyldisilazane, hexamethyldisilazane, etc. into contact with the substrate and subjecting it to plasma polymerization treatment ( JP-A-9-143289).
  • a plasma polymerizable silazane compound gas such as dimethyldisilazane, tetramethyldisilazane, hexamethyldisilazane, etc.
  • the thickness of the formed gas barrier layer is preferably 20 nm to 100 ⁇ m, more preferably 30 to 500 nm, and still more preferably 40 to 200 nm.
  • the adhesive sheet which has sufficient gas barrier performance can be obtained.
  • the surface layer portion of the gas barrier layer in the present invention refers to the surface of the gas barrier layer and a region from the surface to a depth of 5 nm.
  • the surface of the gas barrier layer includes the boundary surface when forming a boundary surface with another layer.
  • the existence ratio of oxygen atoms, nitrogen atoms, and silicon atoms in the surface layer portion of the gas barrier layer is determined by performing elemental analysis of the surface layer portion of the gas barrier layer near 5 nm from the surface using X-ray photoelectron spectroscopy (XPS). Can be confirmed. Specifically, it is measured by the method described in the examples.
  • the proportion of oxygen atoms present is 60 to 75%, the proportion of nitrogen atoms is 0 to 10%, and the presence of silicon atoms with respect to the total amount of oxygen atoms, nitrogen atoms and silicon atoms in the surface layer portion of the gas barrier layer of the present invention.
  • the proportion is 25 to 35%, preferably the proportion of oxygen atoms is 60 to 72%, the proportion of nitrogen atoms is 0.1 to 8.0%, and the proportion of silicon atoms is 27 to 35%.
  • the film density in the surface layer portion of the gas barrier layer of the present invention is 2.4 to 4.0 g / cm 3 from the viewpoint of improving gas barrier properties, bending resistance and transparency, but preferably 2.45 to 4 0.0 g / cm 3 , more preferably 2.5 to 4.0 g / cm 3 .
  • the film density is less than 2.4 g / cm 3, a particular result gas barrier properties of the adhesive sheet is poor.
  • the film density can be calculated using an X-ray reflectivity method (XRR).
  • X-rays are totally reflected when they are incident on the thin film on the substrate at a very shallow angle.
  • XRR X-ray reflectivity method
  • XRR X-ray reflectivity method
  • x-rays penetrate into the thin film and are divided into transmitted waves and reflected waves at the thin film surface and interface, and the reflected waves interfere.
  • the density of the film can be obtained.
  • the thickness of the thin film can also be obtained from measurement while changing the incident angle and analyzing the interference signal of the reflected wave accompanying the change in the optical path difference.
  • the film density can be measured by the following method. In general, it is known that the refractive index n of a substance with respect to X-rays and ⁇ of the real part of the refractive index n are expressed by the following equations 1 and 2.
  • the r e is the electron classical radius (2.818 ⁇ 10 -15 m)
  • a N o is Avogadro's number
  • a wavelength of ⁇ is X-ray
  • [rho is the density (g / cm 3)
  • Z i , M i and x i respectively represent the atomic number, atomic weight and atomic number ratio (molar ratio) of the i-th atom
  • f i ′ represents the atomic scattering factor (anomalous dispersion term) of the i-th atom.
  • the total reflection critical angle ⁇ c is given by Equation 3 when ⁇ related to absorption is ignored, and the density ⁇ can be obtained by Equation 4 from the relationship of Equations 2 and 3.
  • ⁇ c is a value that can be obtained from the X-ray reflectivity
  • r e , N o , and ⁇ are constants
  • Z i , M i , and f i ′ are values specific to the constituent atoms.
  • x i atomic number ratio (molar ratio)
  • the result obtained from the XPS measurement is used.
  • the film density in the surface part of the gas legislation layer is measured by the method described in Examples, and is obtained using Equation 4.
  • the gas barrier layer of the present invention is preferably adjusted so as to satisfy the above requirements (b) and (c) by implanting ions. Therefore, it is preferable that ions are implanted into the gas barrier layer of the pressure-sensitive adhesive sheet of the present invention.
  • the timing for implanting ions is not particularly limited. For example, there is a procedure in which a gas barrier layer is formed on a substrate and then ions are implanted into the gas barrier layer.
  • Implanted ions include those obtained by ionizing rare gases such as argon, helium, neon, krypton, and xenon; ions obtained by ionizing gases such as fluorocarbon, hydrogen, nitrogen, oxygen, carbon dioxide, chlorine, fluorine, and sulfur. And metal ions such as gold, silver, copper, platinum, nickel, palladium, chromium, titanium, molybdenum, niobium, tantalum, tungsten, and aluminum.
  • rare gases such as argon, helium, neon, krypton, and xenon
  • ions obtained by ionizing gases such as fluorocarbon, hydrogen, nitrogen, oxygen, carbon dioxide, chlorine, fluorine, and sulfur.
  • metal ions such as gold, silver, copper, platinum, nickel, palladium, chromium, titanium, molybdenum, niobium, tantalum, tungsten, and aluminum.
  • a pressure-sensitive adhesive sheet that can be more easily injected and has particularly excellent gas barrier properties and transparency
  • a gas in which at least one selected gas is ionized is preferable.
  • the ion implantation amount is appropriately determined in consideration of the purpose of use of the pressure-sensitive adhesive sheet (necessary gas barrier properties, transparency, etc.).
  • conditions for implanting ions known ones can be used, and examples include the conditions described in the examples.
  • Examples of the ion implantation method include a method of irradiating ions accelerated by an electric field (ion beam), a method of implanting ions in plasma (plasma ion implantation method), and the like.
  • plasma ion implantation method are preferable.
  • a plasma is generated in an atmosphere containing a plasma generation gas, and a negative high voltage pulse is applied to the gas barrier layer, so that ions (positive ions) in the plasma are changed to the surface of the gas barrier layer. It can be performed by injecting into the part.
  • the thickness of the portion into which ions are implanted can be controlled by the implantation conditions such as ion type, applied voltage, treatment time, etc., and may be determined according to the thickness of the gas barrier layer, the purpose of use of the adhesive sheet, and the like.
  • the thickness of the portion into which ions are implanted is preferably 10 to 1000 nm, more preferably 10 to 500 nm, and still more preferably 10 to 250 nm.
  • Adhesive layer It does not specifically limit as an adhesive which forms an adhesive layer, For example, what is used normally, for example, an acrylic adhesive, a rubber adhesive, a polyurethane adhesive, a silicone adhesive, etc. are mentioned.
  • the acrylic pressure-sensitive adhesive is not particularly limited. For example, a (meth) acrylic acid ester homopolymer, a copolymer containing two or more (meth) acrylic acid ester units, and a (meth) acrylic acid ester and others. And those containing at least one selected from copolymers with functional monomers.
  • “(Meth) acrylic acid” means acrylic acid or methacrylic acid (the same applies hereinafter).
  • (meth) acrylic acid ester (meth) acrylic acid having 1 to 20 carbon atoms in the alkyl group is preferable, and butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, (meth ) Heptyl acrylate, octyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, and the like.
  • rubber-based pressure-sensitive adhesives include natural rubber, modified natural rubber obtained by graft polymerization of one or more monomers selected from (meth) acrylic acid alkyl ester, styrene, and (meth) acrylonitrile on natural rubber. And rubber adhesives made of styrene-butadiene rubber, acrylonitrile-butadiene rubber, methyl methacrylate-butadiene rubber, urethane rubber, polyisobutylene resin, polybutene resin, and the like.
  • a rubber-based pressure-sensitive adhesive is preferable from the viewpoint of suppressing the permeation of water vapor from the end of the formed pressure-sensitive adhesive layer, and a pressure-sensitive adhesive containing a polyisobutylene resin is used. More preferably, a pressure-sensitive adhesive containing both a polyisobutylene resin and a polybutene resin is more preferable.
  • the polyisobutylene-based resin is a resin having a polyisobutylene skeleton in the main chain or side chain, a resin having the following structural unit (a), and is a homopolymer of isobutylene, polyisobutylene, isobutylene and isoprene, isobutylene and n A copolymer of butene or isobutylene and butadiene, a halogenated butyl rubber obtained by brominating or chlorinating these copolymers, and the like.
  • the polyisobutylene resin is a copolymer obtained from isobutylene and n-butene
  • isobutylene is the maximum amount of monomer as a main component in the raw material monomers.
  • Polyisobutylene resins may be used alone or in combination of two or more.
  • the weight average molecular weight of the polyisobutylene resin is preferably 200,000 to 1,000,000, more preferably 250,000 to 800,000, still more preferably 300,000 to 500,000. If it is 200,000 or more, sufficient cohesive force of the adhesive composition can be obtained. Moreover, if it is 1 million or less, the cohesive force of the pressure-sensitive adhesive composition will not be too high, and sufficient wettability with the adherend will be obtained. Also, when preparing the pressure-sensitive adhesive, It can be dissolved sufficiently. Therefore, by selecting an appropriate molecular weight, the water vapor transmission rate is low, and high cohesion and wettability can be maintained. In addition, this weight average molecular weight (Mw) is a value in terms of polystyrene measured by gel permeation chromatography (GPC) method (hereinafter the same).
  • Polybutene resin is a copolymer having a long-chain hydrocarbon molecular structure.
  • the polybutene copolymer is a copolymer of isobutene, 1-butene, and 2-butene, and among these, an isobutene-1-butene copolymer is preferable.
  • Polybutene resins may be used alone or in combination of two or more. This polybutene resin is well compatible with the polyisobutylene resin and appropriately plasticizes the polyisobutylene resin to improve the wettability with respect to the adherend and improve the adhesive properties, flexibility, holding power, etc. Is for.
  • the weight average molecular weight of the polybutene resin is preferably 500 to 100,000, more preferably 1000 to 50,000, and still more preferably 3,000 to 10,000. If it is 500 or more, it is possible to prevent the possibility of adversely affecting the physical properties such as contamination of the adherend by separation as a low molecular component and increase of outgas generated at high temperature. Also, if 100,000 or less, it is possible to obtain a sufficient plasticizing effect, wetting of the adherend is sufficient.
  • the weight average molecular weight is a value in terms of polystyrene as measured by gel permeation chromatography (GPC).
  • the content of the polybutene resin is preferably 10 to 100 parts by mass, more preferably 15 to 100 parts by mass, and further preferably 25 to 100 parts by mass with respect to 100 parts by mass of the polyisobutylene resin.
  • a hindered amine light stabilizer as a light stabilizer and a hindered phenol-based oxidation as an antioxidant.
  • An inhibitor may be included. You may use a hindered amine light stabilizer and a hindered phenolic antioxidant individually or in combination of 2 or more types.
  • hindered amine light stabilizer examples include dimethyl succinate-1- (2-hydroxyethyl) -4-hydroxy-2,2,6,6-tetramethylpiperidine polycondensate, poly [ ⁇ 6- (1,1,3,3? Tetramethylbutyl) amino-1,3,5?
  • hindered phenol antioxidant examples include triethylene glycol-bis [3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate], 1,6-hexanediol-bis. [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], pentaerythrityl tetrakis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], 2 , 2-thio-diethylenebis [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate], octadecyl-3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionate N, N′-hexamethylenebis (3,5-di-tert-butyl-4-hydroxy-hydroxynnamamide, 1,3,5-trimethyl 2,4,6-tris (3,5-di-t-butyl-4-hydroxy
  • the content of the hindered amine light stabilizer is preferably 0.25 to 1.0 part by weight, more preferably 0.4 to 1.0 part by weight, based on 100 parts by weight of the polyisobutylene resin.
  • the content of the hindered phenol-based antioxidant is preferably 0.25 to 1.0 part by weight, more preferably 0.4 to 1.0 part by weight with respect to 100 parts by weight of the polyisobutylene resin. is there.
  • the pressure-sensitive adhesive composition used in the present invention may further contain a cyclic olefin polymer.
  • the cyclic olefin-based polymer is useful for the purpose of adjusting the viscosity at the time of coating, improving the flexibility due to the plastic effect, improving the initial adhesive force by improving the wettability, and increasing the cohesive force. Moreover, the point with a low water vapor transmission rate is also preferable.
  • the cyclic olefin polymer is meant a polymer containing repeating units derived from cycloolefin monomers.
  • the bonding mode of the cyclic olefin monomer is not particularly limited as long as a cyclic structure can be introduced into the main chain.
  • Examples of the cyclic olefin polymer include those obtained by polymerizing the carbon-carbon unsaturated bond of the monomer, those obtained by addition polymerization of a cyclic conjugated diene, and more specifically, alicyclic having a norbornene ring. Ring-opening polymer obtained by ring-opening polymerization of an alicyclic monomer having a norbornene ring. Or addition polymerization of a monocyclic olefin monomer, or 1,4-addition polymerization of a cyclic conjugated diene monomer such as cyclopentadiene or cyclohexadiene, or a monocyclic olefin monomer.
  • Examples include those obtained by copolymerizing a monomer and a cyclic conjugated diene monomer and a copolymerizable monomer other than the cyclic olefin. Further, these polymers may be further hydrogenated, and specific examples include so-called hydrogenated petroleum resins obtained by hydrogenating petroleum resins known as tackifiers. Examples of hydrogenated petroleum resins include partially hydrogenated resins having different hydrogenation rates, and fully hydrogenated resins. Compatibility with the polyisobutylene resin and the polybutene resin, water vapor transmission rate, high From the viewpoint of durability against wet heat and ultraviolet rays, a completely hydrogenated resin is preferred. In addition, you may use these cyclic olefin type polymers individually or in combination of 2 or more types.
  • the weight average molecular weight of the cyclic olefin polymer is preferably from 200 to 5,000, more preferably from 500 to 3,000, from the viewpoints of adhesion, wetting with the adherend, and compatibility with the polyisobutylene resin.
  • the content of the cyclic olefin polymer is preferably 10 to 300 parts by mass, more preferably 10 to 100 parts by mass with respect to 100 parts by mass of the polyisobutylene resin from the viewpoints of tackiness and wetting with the adherend. It is.
  • the pressure-sensitive adhesive used in the present invention includes, as far as other additives are added, a light stabilizer, an antioxidant, an ultraviolet absorber, a resin stabilizer, a filler, a pigment, and an extender, as long as the adhesiveness is not impaired. Further, it may contain an antistatic agent, a tackifier, and the like. These additives may be used alone or in combination of two or more.
  • the thickness of the pressure-sensitive adhesive layer is not particularly limited and may be appropriately selected depending on the use of the pressure-sensitive adhesive sheet, but is preferably 0.5 to 100 ⁇ m, more preferably 1 to 60 ⁇ m, and still more preferably 3 to 40 ⁇ m. It is. If it is 0.5 ⁇ m or more, good adhesive force can be obtained for the adherend, and if it is 100 ⁇ m or less, it is advantageous in terms of productivity and can be an easy-to-handle pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive composition can be produced by a known coating method as a solution in which the pressure-sensitive adhesive composition is dissolved in an organic solvent such as toluene, ethyl acetate, or methyl ethyl ketone.
  • concentration of the solution is preferably 10 to 60% by mass, more preferably 10 to 30% by mass.
  • Examples of the coating method include spin coating, spray coating, bar coating, knife coating, roll coating, blade coating, die coating, and gravure coating. After applying a solution in which the above-mentioned adhesive is dissolved in an organic solvent to the release layer surface of the substrate or release sheet by these coating methods, a temperature of 80 to 150 ° C. is used to prevent the solvent and low-boiling components from remaining. Can be heated and dried for 30 seconds to 5 minutes to form an adhesive layer.
  • a release sheet can be further provided on the formed pressure-sensitive adhesive layer as desired.
  • the adhesive sheet of this invention what laminated
  • the release sheet may be in the outermost layer of the layer constituting the pressure-sensitive adhesive sheet, or the pressure-sensitive adhesive layer formed on the release sheet having releasability on both sides It may be in the form of being laminated and wound up as it is.
  • the release sheet examples include paper substrates such as glassine paper, coated paper, and high-quality paper, laminated paper obtained by laminating a thermoplastic resin such as polyethylene or polypropylene on these paper substrates, and cellulose, starch A paper base material treated with polyvinyl alcohol, acrylic-styrene resin or the like, or a polyester film such as polyethylene terephthalate, polybutylene terephthalate or polyethylene naphthalate, a plastic film such as a polyolefin film such as polyethylene or polypropylene, and Examples include those obtained by applying a release agent to a film obtained by subjecting these plastic films to an easy adhesion treatment, and forming a release agent layer.
  • release agent examples include rubber elastomers such as olefin resins, isoprene resins, butadiene resins, long chain alkyl resins, alkyd resins, fluorine resins, silicone resins, and the like.
  • the thickness of the release agent layer formed on the substrate of the release sheet is not particularly limited. However, when a solution prepared by dissolving the release agent in the above organic solvent is applied on the substrate, it is preferably 0. .05 to 2.0 ⁇ m, more preferably 0.1 to 1.5 ⁇ m. On the other hand, when the release agent layer is formed using a thermoplastic resin such as polyethylene or polypropylene, the thickness of the release agent layer is preferably 3 to 50 ⁇ m, more preferably 5 to 40 ⁇ m.
  • the water vapor transmission rate at a thickness of 50 ⁇ m of the pressure-sensitive adhesive layer of the pressure-sensitive adhesive sheet of the present invention is preferably 25 g / m 2 / day or less, more preferably 10 g / m 2 / day or less in an atmosphere of 40 ° C. and relative humidity 90%. More preferably, it is 8 g / m 2 / day or less. If the water vapor transmission rate is 25 g / m 2 / day or less, water intrusion from the end of the pressure-sensitive adhesive layer can be prevented, so that it can also be suitably used for sealing organic EL elements. Further, the adhesive strength of the adhesive sheet of the present invention, even when a small thickness of the adhesive layer, has a high adhesive force.
  • the adhesive strength of the adhesive sheet of the present invention is preferably 3N / 25 mm or more, more preferably 5N / 25 mm or more.
  • the adhesive strength of the adhesive sheet of the present invention means a value measured by the method described in Example.
  • the pressure-sensitive adhesive sheet of the present invention can be provided with other layers other than the above (1) to (3).
  • examples of other layers include an inorganic compound layer, a shock absorbing layer, a conductor layer, and a primer layer.
  • stacked is not specifically limited, According to the role of each layer, it selects suitably.
  • An inorganic compound layer is a layer which consists of 1 type, or 2 or more types of an inorganic compound, and can further improve the gas barrier property of an adhesive sheet.
  • the inorganic compound that constitutes the inorganic compound layer is generally capable of vacuum film formation and has a gas barrier property, such as an inorganic oxide, an inorganic nitride, an inorganic carbide, an inorganic sulfide, or a composite of these.
  • gas barrier property such as an inorganic oxide, an inorganic nitride, an inorganic carbide, an inorganic sulfide, or a composite of these.
  • examples thereof include nitrides, inorganic oxide carbides, inorganic nitride carbides, and inorganic oxynitride carbides.
  • inorganic oxides, inorganic nitrides, and inorganic oxynitrides are preferable.
  • Examples of inorganic oxides include metal oxides represented by the general formula: MOx.
  • M represents a metal element.
  • x has a different range depending on M. For example, if M is silicon (Si), 0.1 to 2.0, if aluminum (Al), 0.1 to 1.5, and if magnesium (Mg), 0.1 to 1.0, 0.1 to 1.0 for calcium (Ca), 0.1 to 0.5 for potassium (K), 0.1 to 2 for tin (Sn) 0.0, 0.1 to 0.5 for sodium (Na), 0.1 to 1.5 for boron (B), 0.1 to 2.0 for titanium (Ti), lead ( The value is in the range of 0.1 to 1.0 for Pb), 0.1 to 2.0 for zirconium (Zr), and 0.1 to 1.5 for yttrium (Y).
  • silicon oxide in which M is silicon, aluminum oxide in aluminum, and titanium oxide in titanium are preferable, and silicon oxide is more preferable.
  • the value of x is 1.0 to 2.0 when M is silicon and 0.5 to 1.5 when aluminum is used from the viewpoint of forming a layer having excellent transparency and the like. If so, the range of 1.3 to 2.0 is preferable.
  • Examples of inorganic nitrides include metal nitrides represented by the general formula: MNy.
  • M represents a metal element.
  • silicon nitride where M is silicon, aluminum nitride which is aluminum, titanium nitride which is titanium, and tin nitride which is tin are preferable.
  • Nitride (SiN) is more preferred.
  • titanium 0.5 to 1.3 is preferable
  • tin 0.5 to 1.3 is preferable.
  • Examples of the inorganic oxynitrides include metal oxynitrides represented by the general formula: MOxNy.
  • M represents a metal element.
  • the metal oxide, a metal nitride and a metal oxynitride may also contain two or more metals.
  • the method for forming the inorganic compound layer is not particularly limited, and examples thereof include a vapor deposition method, a sputtering method, an ion plating method, a thermal CVD method, a plasma CVD method, and a dynamic ion mixing method.
  • a magnetron sputtering method is preferable because a laminate having an excellent gas barrier property can be easily obtained.
  • the thickness of the inorganic compound layer is not particularly limited, but is preferably 10 to 1000 nm, more preferably 20 to 500 nm, and still more preferably 50 to 200 nm from the viewpoint of improving gas barrier properties.
  • the shock absorbing layer is for preventing cracking when an impact is applied to the gas barrier layer or the inorganic compound layer, and the material for forming the shock absorbing layer is not particularly limited. Resins, urethane resins, silicone resins, olefin resins, rubber materials, and the like can be used. Among these, acrylic resins, silicone resins, and rubber materials are preferable.
  • acrylic resins As acrylic resins, (meth) acrylic acid ester homopolymers, copolymers containing two or more (meth) acrylic acid ester units, and (meth) acrylic acid esters and other functional monomers are used as main components. What contains at least 1 sort (s) chosen from the copolymer with a monomer is mentioned.
  • (meth) acrylic acid ester As the (meth) acrylic acid ester, (meth) acrylic acid having 1 to 20 carbon atoms in the ester portion is preferable, and (meth) acrylic acid ester having 4 to 10 carbon atoms in the ester portion is more preferable.
  • Such (meth) acrylic acid esters include butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, (meth) Examples include 2-ethylhexyl acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, and the like.
  • silicone resin examples include those containing dimethylsiloxane as a main component.
  • the rubber-based material examples include materials mainly composed of isoprene rubber, styrene-butadiene rubber, polyisobutylene rubber, styrene-butadiene-styrene rubber and the like.
  • the raw material which forms a shock absorption layer can also use what is marketed.
  • the impact absorbing layer may contain other additives such as other components such as an antioxidant, a plasticizer, an ultraviolet absorber, a colorant, and an antistatic agent.
  • the shock absorption layer containing the raw material which forms the said shock absorption layer, and other components, such as a solvent if desired, similarly to the formation method of an adhesive layer
  • examples include a method in which a forming solution is applied onto a layer to be laminated, the obtained coating film is dried, and heated to form the film as necessary.
  • a shock absorbing layer may be separately formed on the release substrate, and the obtained film may be transferred and stacked on the layer to be stacked.
  • the thickness of the shock absorbing layer is usually 1 to 100 ⁇ m, preferably 5 to 50 ⁇ m.
  • a conductor layer is a layer provided in order to give electroconductivity, when providing antistatic performance, or when using an adhesive sheet as an electrode.
  • Examples of the material constituting the conductor layer include metals, alloys, metal oxides, electrically conductive compounds, and mixtures thereof.
  • tin oxide (ATO) doped with antimony tin oxide (FTO) doped with fluorine
  • conductive such as tin oxide, zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO) Metal such as gold, silver, chromium and nickel; mixtures of these metals and conductive metal oxides; inorganic conductive materials such as copper iodide and copper sulfide; organic conductive materials such as polyaniline, polythiophene and polypyrrole Materials and the like.
  • the conductor layer may be a laminate in which a plurality of layers made of these materials are laminated. Among these, in terms of transparency, a conductive metal oxide is preferable, and ITO is more preferable.
  • Examples of the method for forming the conductor layer include a vapor deposition method, a sputtering method, an ion plating method, a thermal CVD method, a plasma CVD method, and the like.
  • the sputtering method is preferable because the conductor layer can be easily formed.
  • the sputtering method introduces a discharge gas (such as argon) into a vacuum chamber, applies a high-frequency voltage or a direct current voltage between the target and the substrate to turn the discharge gas into plasma, and collides the plasma with the target material.
  • a discharge gas such as argon
  • This is a method of obtaining a thin film by skipping and attaching to a substrate.
  • a target made of a material for forming the conductor layer is used as the target.
  • the thickness of the conductor layer may be appropriately selected depending on the application and the like, but is usually 10 nm to 50 ⁇ m, preferably 20 nm to 20 ⁇ m.
  • the surface resistivity of the obtained conductor layer is usually 1000 ⁇ / ⁇ or less.
  • the formed conductor layer may be patterned as necessary.
  • the patterning method include chemical etching by photolithography and the like, physical etching using a laser and the like, vacuum deposition method using a mask, sputtering method, lift-off method, printing method, and the like.
  • Primer layer plays the role which improves the interlayer adhesiveness with a base material layer, a gas barrier layer, an adhesive layer, or another layer.
  • a pressure-sensitive adhesive sheet having excellent interlayer adhesion and surface smoothness can be obtained.
  • the material constituting the primer layer is not particularly limited, and known materials can be used.
  • a silicon-containing compound a polymerizable composition comprising a photopolymerizable compound comprising a photopolymerizable monomer and / or a photopolymerizable prepolymer, and a polymerization initiator that generates radicals at least in the visible light region; a polyester resin , Polyurethane resins (particularly polyacrylic polyols, polyester polyols, polyether polyols and isocyanate compounds) and acrylic resins, polycarbonate resins, vinyl chloride / vinyl acetate copolymers, polyvinyl butyral resins And resins such as nitrocellulose-based resins; alkyl titanates; and ethyleneimine.
  • These materials can be used alone or in combination of two or more.
  • a primer layer forming solution obtained by dissolving or dispersing the material constituting the primer layer in an appropriate solvent is applied to one or both sides of the layer to be formed, and the resulting coating film is dried. It can be formed by heating if desired.
  • a normal wet coating method can be used as a method for applying the primer layer forming solution to the layer to be formed. Examples include dipping method, roll coating, gravure coating, knife coating, air knife coating, roll knife coating, die coating, screen printing method, spray coating, gravure offset method and the like.
  • a conventionally known drying method such as hot air drying, hot roll drying, infrared irradiation or the like can be employed.
  • the thickness of the primer layer is usually 10 to 1000 nm.
  • ion implantation may be performed on the obtained primer layer by a method similar to the method of implanting ions into the gas barrier layer described above. By performing ion implantation also on the primer layer, a pressure-sensitive adhesive sheet with better gas barrier properties can be obtained.
  • the shape of the pressure-sensitive adhesive sheet of the present invention is not particularly limited, and examples thereof include a sheet shape. When used as an electronic device member to be described later, a sheet shape is preferable.
  • the visible light transmittance of the pressure-sensitive adhesive sheet of the present invention at a wavelength of 550 nm is preferably 85% or more, more preferably 88% or more, and still more preferably 90% or more. If the visible light transmittance is 85% or more, it can be suitably used as an electronic device member to be described later, for example, as a sealing application in an organic EL element.
  • permeability of an adhesive sheet can be measured using a well-known visible light transmittance
  • the water vapor transmission rate of the entire pressure-sensitive adhesive sheet of the present invention having the gas barrier layer and the pressure-sensitive adhesive layer described above is preferably 1.0 g / m 2 / day or less, more preferably 0 in an atmosphere of 40 ° C. and a relative humidity of 90%. .5g / m 2 / day, more preferably not more than 0.1g / m 2 / day.
  • the adhesive sheet of this invention is excellent in bending resistance as above-mentioned, even if it performs bending etc., gas barrier property can be maintained.
  • the water vapor permeability of the entire pressure-sensitive adhesive sheet after the bending test described in the examples is preferably 1.0 g / m 2 / day or less, more preferably 0.5 g in an atmosphere of 40 ° C. and a relative humidity of 90%. / M 2 / day or less, more preferably 0.1 g / m 2 / day or less.
  • the pressure-sensitive adhesive sheet of the present invention can be used as an electronic device member, for example, for sealing organic EL elements. Since the pressure-sensitive adhesive sheet of the present invention has excellent gas barrier properties and the like, for example, it is possible to prevent deterioration of organic EL elements and the like used in electronic devices.
  • FIG. 2 the example of the organic EL element using the adhesive sheet of this invention is shown.
  • the organic EL element 10 a structure 14 in which a transparent electrode, a hole transport layer, a light emitting layer, a back electrode, and the like are laminated on a glass substrate 12 is formed.
  • the pressure-sensitive adhesive sheet 1 of the present invention has a configuration in which a gas barrier layer 3 and a pressure-sensitive adhesive layer 4 are laminated on a base material 2.
  • the structure 14 is sealed.
  • the organic EL element 10 is sealed by attaching the adhesive sheet 16 of the present invention after forming the structure 14 on the glass substrate 12. According to the pressure-sensitive adhesive sheet of the present invention, the element can be easily sealed.
  • the electronic device of this invention is equipped with the adhesive sheet of this invention as a member for electronic devices. Since the pressure-sensitive adhesive sheet of the present invention has excellent gas barrier properties, transparency, bending resistance, etc., it can be used for various electronic devices. Examples of the electronic device of the present invention include a liquid crystal display, an organic EL display, an inorganic EL display, electronic paper, and a solar battery.
  • Plasma ion implantation apparatus used XPS measurement apparatus, film density measurement apparatus by X-ray reflectivity method, bending test method, water vapor transmission rate measurement apparatus and measurement conditions, water vapor transmission test method at end of adhesive layer, adhesion
  • the force measuring method and the visible light transmittance measuring device are as follows.
  • RF power source JEOL Ltd., model number “RF” 56000
  • High voltage pulse power supply “PV-3-HSHV-0835” manufactured by Kurita Manufacturing Co., Ltd.
  • the plasma ion implantation apparatus used is an apparatus for implanting ions using an external electric field. The conditions for plasma ion implantation are shown below.
  • Plasma generated gas Ar ⁇ Gas flow rate: 100sccm ⁇ Duty ratio: 0.5% ⁇ Repetition frequency: 1000Hz ⁇ Applied voltage: -10kV -RF power supply: frequency 13.56 MHz, applied power 1000 W -Chamber internal pressure: 0.2 Pa ⁇ Pulse width: 5 ⁇ sec ⁇ Processing time (ion implantation time): 5 minutes ⁇ Conveying speed: 0.2 m / min
  • XPS measuring device An XPS measurement device is measured by elemental analysis by X-ray photoelectron spectroscopy (XPS) to measure the abundance ratio of oxygen atoms, nitrogen atoms, and silicon atoms in the surface layer portion (around 5 nm from the surface) of the gas barrier layer. Used.
  • the measurement equipment and measurement conditions are as follows. Measuring device: “PHI Quantera SXM”
  • ULVAC-PHI X-ray source AlK ⁇ X-ray beam diameter: 100 ⁇ m
  • Electric power value 25W Voltage: 15kV Extraction angle: 45 ° Degree of vacuum: 5.0 ⁇ 10 ⁇ 8 Pa
  • the film density in the surface layer portion of the gas barrier layer was calculated from the total reflection critical angle ⁇ c obtained by measuring the X-ray reflectivity under the following measurement conditions.
  • the measurement equipment and measurement conditions are as follows.
  • Measuring device Sample horizontal X-ray diffractometer for thin film evaluation “SmartLab” manufactured by Rigaku Corporation Measurement conditions: X-ray source; Cu-K ⁇ 1 (wavelength; 1.54059 mm)
  • Optical system Parallel beam optical system Incident side slit system: Ge (220) 2 crystal, height limiting slit 5 mm, incident slit 0.05 mm
  • Light receiving slit system Light receiving slit 0.10mm, solar slit 5 ° Detector; Scintillation counter Tube voltage and tube current; 45kV-200mA Scanning axis; 2 ⁇ / ⁇ Scan mode: continuous scan Scan range: 0.1-3.0 deg. Scanning speed; ldeg. / Min.
  • the atomic ratio (x i in the above formula 4) used the abundance ratio of oxygen atoms, nitrogen atoms and silicon atoms in the surface layer portion of the gas para layer obtained by X-ray photoelectron spectroscopy measurement.
  • Water vapor permeability measuring device and measurement conditions When the water vapor transmission rate is 0.01 g / m 2 / day or more, a water vapor transmission meter (manufactured by LYSSY, product name “L89-500”) is used, and the water vapor transmission rate is less than 0.01 g / m 2 / day.
  • the water vapor transmission rate of the pressure-sensitive adhesive sheet (“water vapor transmission rate before bending” in Table 1) was measured under the conditions of 40 ° C. and relative humidity of 90% using “deltaperm” manufactured by TECHNOLOX. Further, the water vapor transmission rate of the pressure-sensitive adhesive sheet after the bending test (“water vapor transmission rate after bending” in Table 1) was also measured in the same manner.
  • PET 6 ⁇ m polyethylene terephthalate film (manufactured by Mitsubishi Plastics, trade name“ K200-6E ”, thickness 6 ⁇ m) (hereinafter also referred to as“ PET 6 ⁇ m ”)” It stuck on both surfaces and measured by the structure of PET6micrometer / adhesive layer 50micrometer / PET6micrometer.
  • the pressure-sensitive adhesive sheet for the water vapor permeation test at the edge of the pressure-sensitive adhesive was cut into a frame shape having an outer dimension of 60 mm ⁇ 60 mm and a width of 2 mm, the light release sheet was peeled off, and affixed to a 70 mm ⁇ 70 mm ⁇ 2 mm thick glass plate. Next, the heavy release sheet is peeled off, a humidity indicator seal (product name “RH-70”, manufactured by Asei Kogyo Co., Ltd.) is attached to the inside of the frame of the adhesive sheet, and then attached to another glass plate. The space was sealed with two glass plates and an adhesive sheet.
  • a humidity indicator seal product name “RH-70”, manufactured by Asei Kogyo Co., Ltd.
  • the prepared specimen was left in an atmosphere of 60 ° C. and a relative humidity of 90%, and then the humidity in the frame was evaluated.
  • the humidity indicator used is colored from white to blue at a relative humidity of 70%, and the accuracy is ⁇ 5% RH (RH: relative humidity) at 25 ° C.
  • the evaluation criteria are as shown below. ⁇ : No color change of humidity indicator seal ⁇ : There is a slight color change of humidity indicator seal
  • the visible light transmittance (%) of the pressure-sensitive adhesive sheet was measured at a measurement wavelength of 550 nm using a visible light transmittance measuring device (manufactured by Shimadzu Corporation, “UV-3101PC”).
  • Polysilazane compound A Coating material mainly composed of perhydropolysilazane (trade name “AQUAMICA NL110-20” manufactured by Clariant Japan Co., Ltd.)
  • Polysilazane compound B a coating material mainly composed of a mixture of organopolysilazane compounds having a saturated hydrocarbon group (manufactured by Clariant Japan, trade name “tutoPromBright”)
  • polysilazane compound A As a substrate, polysilazane compound A was applied by spin coating to a polyethylene terephthalate film (Mitsubishi Resin, “PET38 T-100”, thickness 38 ⁇ m, hereinafter referred to as “PET film”), and then at 120 ° C. for 1 minute. A 60 nm thick polysilazane layer containing perhydropolysilazane was formed on the PET film by heating. Next, argon (Ar) was plasma ion-implanted into the surface of the layer containing perhydropolysilazane using a plasma ion implantation apparatus to produce “a substrate with a gas barrier layer 1”.
  • argon (Ar) was plasma ion-implanted into the surface of the layer containing perhydropolysilazane using a plasma ion implantation apparatus to produce “a substrate with a gas barrier layer 1”.
  • a “base material with a gas barrier layer 11” was obtained in the same manner as in Production Example 2 except that oxygen (O 2 ) was used instead of argon as the plasma generation gas.
  • a “base material with a gas barrier layer 12” was obtained in the same manner as in Production Example 2 except that helium (He) was used instead of argon as the plasma generation gas.
  • a “base material with a gas barrier layer 13” was obtained in the same manner as in Production Example 2, except that neon (Ne) was used instead of argon as the plasma generation gas.
  • Examples 1 to 22, Comparative Examples 1 to 3 Using the pressure-sensitive adhesive composition obtained as described above and the base material with a gas barrier layer obtained in Production Examples 1 to 17, the pressure-sensitive adhesive sheets of Examples 1 to 22 and Comparative Examples 1 to 3 were as follows. It produced as follows. Combinations of the pressure-sensitive adhesive composition and the base material with the gas barrier layer are as shown in Table 1.
  • the pressure-sensitive adhesive compositions A to H are applied to the release surface of a light release sheet (trade name “SP-PET1031”, manufactured by Lintec Corporation) using a roll knife coater so that the film thickness after drying becomes 20 ⁇ m. And dried at 100 ° C. for about 1 minute to form an adhesive layer.
  • the gas barrier layer surface of the substrate with the gas barrier layers 1 to 17 was laminated on the pressure-sensitive adhesive surface and bonded to obtain a pressure-sensitive adhesive sheet.
  • the pressure-sensitive adhesive sheet of the example having the gas barrier layer satisfying the above requirements (A) to (C) has a low water vapor transmission rate and high compared to the pressure-sensitive adhesive sheets of Comparative Examples 1 to 3 that do not satisfy the requirement. It had gas barrier properties. Also, in the water vapor permeation test at the end of the pressure-sensitive adhesive layer, there was almost no water intrusion from the end of the pressure-sensitive adhesive layer, and the adhesive strength was sufficient. Further, after the bending test, the pressure-sensitive adhesive sheet of the example showed no occurrence of cracks in the gas barrier layer, but in Comparative Example 3 in which an inorganic film (silicon nitride film) was formed, the occurrence of cracks was seen. . In addition, the pressure-sensitive adhesive sheet of the example had a small increase in water vapor transmission rate as compared with Comparative Example 3, was excellent in bending resistance, and was also excellent in transparency.
  • the pressure-sensitive adhesive sheet of the present invention is an organic transistor, organic memory, electrochromic electronic device, LCD, touch panel, electronic paper display, solar cell photoelectric conversion device, electrochemiluminescence device, thermoelectric conversion device, piezoelectric conversion device, etc. It is useful in various electronic devices.
PCT/JP2011/068651 2010-09-07 2011-08-18 粘着シート、及び電子デバイス WO2012032907A1 (ja)

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US13/820,837 US20130209800A1 (en) 2010-09-07 2011-08-18 Adhesive sheet and electronic device
EP11823386.5A EP2615144B1 (en) 2010-09-07 2011-08-18 Adhesive sheet and electronic device
KR1020137005722A KR101886455B1 (ko) 2010-09-07 2011-08-18 점착 시트 및 전자 디바이스
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KR20140018174A (ko) 2014-02-12
TW201217485A (en) 2012-05-01
TWI504718B (zh) 2015-10-21
EP2615144A4 (en) 2014-10-29
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JPWO2012032907A1 (ja) 2014-01-20
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